The revelations and reversals and clarifications and denials have been spewing nonstop since Rudy Giuliani went on Sean Hannity’s show Wednesday night and casually dropped the bombshell that his new client, President Donald Trump, had indeed reimbursed Michael Cohen for a hush-money payment to porn actress Stormy Daniels. Nutty specifics aside, however, no one who lived through the 90s in New York City should be surprised that Giuliani and Trump have already proved a combustible mix—with Giuliani’s former colleagues being the least surprised, and the most appalled. “This stuff with Trump is a continuation of Rudy’s descent into wackiness,” a former top City Hall aide to Giuliani says. “He always had sort of the wild side, but people would rein him in. Rudy doesn’t have that network now.”
Part of the problem, they point out, is that for all of Giuliani’s strenuous claims of deep friendship with Trump, the two men didn’t have much of a relationship until recently. “You kind of assume they would be close, because they’re cut from the same cloth,” says Andrew Kirtzman, a Giuliani biographer. “Hardscrabble outer-borough white guys who had the same approach to leadership—perpetually on the attack, never give an inch. But they were in different orbits.” (The White House and Giuliani did not immediately respond to a request for comment.)
“I don’t remember Rudy ever speaking to Trump more than a couple of times in the eight years he was mayor,” says the former senior adviser. “They were cordial, but any contact always had to do with transactions—Trump needing a zoning variance, say—not because there was some social link. Trump, to my recollection, did one fund-raiser for Rudy, and Rudy never called Trump for advice or on a regular basis. They had separate circles and were each in the middle of them.”
Things changed in 2016, as Trump closed in on the Republican presidential nomination and Giuliani jumped on the bandwagon, delivering a fire-breathing Republican convention speech attacking Hillary Clinton. Trump was grateful, but not enough to reward Giuliani with the job he wanted, as secretary of state. This morning MSNBC’s Mika Brzezinski said that the president-elect had been wary of the former mayor’s stamina. “During the transition, Donald Trump told both Joe and me that Giuliani was a little out of it, was kind of losing it and would fall asleep—it’s what he told us,” Brzezinski said on Morning Joe. “I don’t know if it played into why he didn’t become secretary of state. We certainly openly lobbied on the air for that not to happen, because we also thought there was something different with him.”
Which squares with what former Giuliani allies have been saying for months. Some of the assessments are political. "He’s gotten more and more extreme in his views, but what’s troubling is the views are also foundationally different than they used to be,” an ex-aide says. “I mean, I cannot imagine the Rudy Giuliani I knew attacking F.B.I. agents. If you told me Rudy was on the wrong side of some racial-discord issue, I wouldn’t be surprised. But the rhetoric on Hillary, the rhetoric on Comey, the sloppiness of his statements on Hannity—that stuff is not recognizable.”
Some see the changes as rooted in Giuliani’s demeanor. “He just doesn’t seem as mentally sharp as he was,” says the former adviser. “It started after 9/11, when he was talking about, ‘I have to take control of the city, we’ve got to change the law, I’m the only one who can save the city.’ He literally thought he was Winston Churchill. It was bizarre. The progression really was after 9/11, and it has continued.”
Giuliani’s grandiosity and megalomania may have worsened, but those qualities weren’t new even in 2001. Whatever may have changed in his personality recently, and whatever the doubts about his legal skills, the one sure thing when Trump hired Giuliani was that Rudy was going to be a high-profile media presence. Way back in 1997, when Giuliani was being mentioned as a vice-presidential possibility on a G.O.P. ticket headed by George W. Bush, his old antagonist Rev. Al Sharpton sized up the situation. “I pity the guy who takes Rudy for vice-anything. He’ll need a food-taster,” Sharpton told New York magazine’s Mark Jacobson. “The minute he gets a head cold, Rudy’ll be calling an act of Congress. Giuliani would make Alexander Haig look bashful.”
Sure enough, Giuliani may have caused his new client some unneeded legal problems this week with his statements—but it was the way Giuliani delivered those statements, on a media blitz, talking about how he will make the decisions regarding a possible presidential interview with Robert Mueller, that could become the real threat to Giuliani’s job security. If there’s one thing Trump can’t tolerate, it’s someone pulling focus away from him.
